Ethanol → 3-Bromo-5-(2,4-difluorophenoxy)aniline

A mixture of 1-(3-bromo-5-nitrophenoxy)-2,4-difluorobenzene (54 mg, 0.16 mmol), ammonium chloride (18 mg, 0.32 mmol), and iron powder (45 mg, 0.80 mmol) suspended in THF (300 uL), water (100 uL) and ethanol (300 uL) was heated to 100° C. using microwave irradiation (normal) for 3 h. The crude reaction mixture was filtered through a short plug of celite; the celite plug was washed with MeOH (˜5 mL). The resulting filtrate was concentrated in vacuo. The resulting residue was diluted with EtOAc (50 ml) and washed with saturated bicarbonate solution (aq), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The crude solid was purified by silica gel column chromatography using a gradient of EtOAc (5 to 20%) in hexanes to afford the title compound (48 mg, 100%) as a yellow solid. LCMS (M+H)+=301.

1. custommicrowave irradiation (normal) for 3 h
2. customThe crude reaction mixture
3. filtrationwas filtered through a short plug of celite
4. washthe celite plug was washed with MeOH (˜5 mL)
5. concentrationThe resulting filtrate was concentrated in vacuo
6. additionThe resulting residue was diluted with EtOAc (50 ml)
7. washwashed with saturated bicarbonate solution (aq)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude solid was purified by silica gel column chromatography

ORD record

ord-1d0405e8a07646388560c69d98aef927

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09115114B2